Synthesis of Functionalized Difluorocyclopropanes: Unique Building Blocks for Drug Discovery

被引:47
作者
Bychek, Roman M. [1 ]
Levterov, Vadym V. [1 ]
Sadkova, Iryna V. [1 ]
Tolmachev, Andrey A. [1 ,2 ]
Mykhailiuk, Pavel K. [1 ,2 ]
机构
[1] Enamine Ltd, Chervonotkatska 78, UA-02094 Kiev, Ukraine
[2] Taras Shevchenko Natl Univ Kyiv, Dept Chem, Volodymyrska 64, UA-01601 Kiev, Ukraine
关键词
amines; cycloaddition; drug discovery; difluorocyclopropane; fluorine; GEM-DIFLUORINATED CYCLOPROPANES; MEDICINAL CHEMISTRY; F-19; NMR; ESCHERICHIA-COLI; MEMBRANE-PROTEIN; FLUORINE; DIFLUOROCARBENE; PROLINE; PEPTIDE; CONFORMATION;
D O I
10.1002/chem.201705708
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Difluorocyclopropane-containing building blocks for drug discovery were synthesized from the functionalized alkenes and TMSCF3/NaI. Novel fluorinated acids, amines, amino acids, alcohols, ketones and sulfonyl chlorides were obtained.
引用
收藏
页码:12291 / 12297
页数:7
相关论文
共 58 条
[51]   Catalytic C-F bond activation of geminal difluorocyclopropanes by nickel(I) complexes via a radical mechanism [J].
Wenz, Jan ;
Rettenmeier, Christoph A. ;
Wadepohl, Hubert ;
Gade, Lutz H. .
CHEMICAL COMMUNICATIONS, 2016, 52 (01) :202-205
[52]  
Xu J., 2015, ANGEW CHEM, V127, P8349
[53]   Pd-Catalyzed Regioselective Activation of gem-Difluorinated Cyclopropanes: A Highly Efficient Approach to 2-Fluorinated Allylic Scaffolds [J].
Xu, Jun ;
Ahmed, Ebrahim-Alkhalil ;
Xiao, Bin ;
Lu, Qian-Qian ;
Wang, Yun-Long ;
Yu, Chu-Guo ;
Fu, Yao .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (28) :8231-8235
[54]   Convenient synthesis of enantiopure (R-) and (S-)-3-fluoro-3-aminomethylpyrrolidines [J].
Yarmolchuk, Vladimir S. ;
Mykhalchuk, Vladimir L. ;
Mykhailiuk, Pavel K. .
TETRAHEDRON, 2014, 70 (18) :3011-3017
[55]   Synthesis and Characterization of β-Trifluoromethyl-Substituted Pyrrolidines [J].
Yarmolchuk, Vladimir S. ;
Shishkin, Oleg V. ;
Starova, Viktoriia S. ;
Zaporozhets, Olga A. ;
Kravchuk, Olga ;
Zozulya, Sergey ;
Komarov, Igor V. ;
Mykhailiuk, Pavel K. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (15) :3086-3093
[56]   Synthesis of β-fluoro-β-proline [J].
Yarmolchuk, Vladimir S. ;
Mykhailiuk, Pavel K. ;
Komarov, Igor V. .
TETRAHEDRON LETTERS, 2011, 52 (12) :1300-1302
[57]   Synthesis of Fused Bicyclic Piperidines: Potential Bioactive Templates for Medicinal Chemistry [J].
Zhou, Jinglan ;
Campbell-Conroy, Erica L. ;
Silina, Alina ;
Uy, Johnny ;
Pierre, Fabrice ;
Hurley, Dennis J. ;
Hilgraf, Nicole ;
Frieman, Bryan A. ;
DeNinno, Michael P. .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01) :70-79
[58]   Trifluorodiazoethane (CF3CHN2) in the Uncatalyzed Cyclopropanation of 3-Arylmethylenebenzofuran-2(3H)-ones [J].
Zhu, Chuan-Le ;
Ma, Jun-An ;
Cahard, Dominique .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (01) :66-69